ABSTRACT Thirteen pentacyclic triterpenes, methyl 3-oxours-12-en-23-oate, marsformosanone, taraxerone, β-amyrenone, α-amyrenone, lupenone, 24-methylencycloartan-3-one, moretenol acetate, β-amyrin acetate, germanicol acetate, 24-methylencycloartanyl acetate, β-amyrin, and α-amyrin were identified in a chloroform-methanol propolis extract from Melipona beecheii. Additionally, were identified in this propolis, hexadecanoic acid, methyl ester, octadecanoic acid, methyl ester and 1-triacontanol. The purification of the propolis extract was carried out using different chromatographic techniques, including vacuum liquid chromatography, gravity column chromatography and gel filtration chromatography Sephadex LH-20. The identification of the metabolites was performed using mass spectrometry.

Abstract: The aim of the study is to investigate anti-inflammatory properties of polar and non-polar extracts prepared from Critoniaaromatisansand Montanoa grandiflora, two common native species used in Mayan traditional ointments to treat inflammation, joint pain and rheumatism. The antiinflammatory properties of methanol/acetonitrile and n- hexane leaf extracts were tested in vivo and in vitro. The extracts of C. aromatisansand M. grandiflora decreased in a concentration-dependent manner lipopolysaccharide (LPS)-induced nitric oxide (NO) production without affecting the cell viability. The extracts of C. aromatisansat dose of 200 mg/kg exhibited substantial anti-inflammatory activity in the carrageenaninduced paw oedema test and 12-O-Tetradecanoylphorbol-13-acetate (TPA)-induced ear oedema inhibition assay with a reduction in inflammation of up to 90 and 80%, respectively. These results validate the traditional uses by Mayan communities that endorse the use of this species to treat inflammation.

Resumen: El objetivo del estudioesinvestigar las propiedadesantiinflamatorias de extractos de Critoniaaromatisansy Montanoa grandiflora, dos especiesnativascomunesutilizadasenungüentostradicionalesmayas para tratar la inflamación, dolor en las articulaciones y el reumatismo. Las propiedadesantiinflamatorias de extractosmetanol/acetonitrilo y n-hexánicos de hojasfueronevaluadosin vitro e in vivo. Los extractos de C. aromatisans y M. grandiflora disminuyeron la producción de óxidonítrico (NO) inducidaporlipopolisacárido (LPS) de maneradependiente de la concentración sin afectar la viabilidadcelular. Los extractos de C. aromatisans, a dosis de 200 mg/kg exhibenactividadantiinflamatoriasustancialen el ensayo de edema plantar inducidoporcarragenina y en el ensayo de inhibición de edema de la orejainducidopor TPA con unareducciónen la inflamación de 90 y 80%, respectivamente. Estosresultadosvalidanlosusostradicionales de las comunidadesmayas que avalan el uso de estaespecie para el tratamiento de la inflamación.

Abstract: The bioassay-guided fractionation of Lonchocarpus punctatus inflorescence extracts led to the purification of the trans (1) and cis (2) isomers of 3,5-dimethoxystilbene, trans-3,4,4’,5-tetramethoxystilbene (3), 4,4’,6’-trimethoxychalcone (4) and 5- hydroxy-7,4’-dimethoxyflavone (5) as their main constituents. the structures of the compounds were established by comparing their nuclear magnetic resonance and mass spectrometry data with that from the literature. among these metabolites, trans-3,4,4’,5-tetramethoxystilbene (3) exhibited potent cytotoxic activity against luminal a (CC50= 2.2 μM), HER2 (CC50= 1.1 μM) and basal triple negative (CC50= 1.8 μM) breast cancer cell lines, but no cytotoxic effects were observed against immortalized hepatocyte cell lines (CC50> 50 μM), and medium (CYP3A4, CYP2C9) and low (CYP2D6) inhibitory properties were observed for P450 isoforms.

Resumen: El fraccionamiento biodirigido de extractos obtenidos de las inflorescencias de Lonchocarpus punctatus Kunth permitieron la purificación de los isómeros trans (1) y cis (2) de 3,5 dimetoxiestilbeno, trans-3,4,4’,5- tetrametoxiestilbeno (3) 4,4’,6’-trimetoxichalcona (4) y 5-hidroxi-7,4’-dimetoxiflavona (5) como sus principales constituyentes. Las estructuras de los compuestos fueron establecidas por comparación de sus datos de resonancia magnética nuclear y espectrometría de masas con los reportados en la literatura. De todos los metabolitos aislados, trans-3,4.4’,5-tetrametoxiestilbeno (3) exhibió potente actividad citotóxica contra las líneas celulares de cáncer luminal a (CC50= 2.2 μM), HEr2 (CC50 = 1.1 μM) y triple negativo basal (CC50= 1.8 μM) pero ningún efecto citotóxico fue observado contra la línea celular inmortalizada de hepatocitos (CC50 > 50 μM), así como propiedades inhibitorias moderadas (CYP3A4, CYP2C9) y bajas (CYP2D6) en las isoformas del citocromo P450.

Background: The whitefly (Bemisia tabaci Genn.) is a widely distributed and highly harmful plant pest species. The management of B. tabaci has been typically carried out by chemical pesticides. In the last decade however, there has been an increasing interest in natural products, particularly those of plant origin, to control this pest species. In the present work, aqueous and ethanolic extracts of native plants from the flora of the Yucatán peninsula (Acalypha gaumeri, Annona squamosa, Carlowrightia myriantha, Petiveria alliaceae and Trichilia arborea) and the introduced plant Azadirachta indica were collected and evaluated for insecticidal activity against eggs and nymphs Bemisia tabaci. Results: Most of the aqueous and ethanolic extracts showed high insecticidal effects on B. tabaci eggs. The lowest LC50 values were recorded in the aqueous extracts of A. gaumeri (0.39% w/v), A. squamosa (0.36% w/v), P. alliaceae (0.42% w/v) and A. indica (0.30% /v), as well as in the ethanolic extracts of P. alliaceae (2.09 mg mL-1) and T. arborea (2.14 mg mL-1). On the other hand, B. tabaci nymphs were not affected by the aqueous extracts, but were highly sensitive to the ethanolic extracts of the tested plants. The lowest LC50 values were recorded in the ethanolic extracts of P. alliaceae (1.27 mg ml-1) and T. arborea (1.61 mg mL-1). The GC-MS analysis showed that phytol was the major component of the ethanolic extract of P. alliaceae and fatty acids were the major components of ethanolic extract of T. arborea. Conclusions: Overall, results suggest that ethanolic extracts of P. alliaceae and T. arborea leaves showed the highest insecticidal effects on eggs and nymphs B. tabaci. The extracts from P. alliaceae and T. arborea are good candidates to be developed as sources of natural insecticides for the management of immature B. tabaci since their effects were comparable with that showed by the extracts of A. indica, a well-known plant species for its insecticidal activity.

Duas novas flavanonas naturais, 5-hidroxi-6,7-(2",2"-dimetilcromeno)flavanone (1) e 5-metoxi-3-hidroxi-6,7-(2",2"-dimetilcromeno)flavanone (2), foram isoladas dos extratos das raízes de L. yucatanensis e L. xuul, respectivamente. Adicionalmente, quatro novos metabólitos, os flavanóides glicosídicos quercetina-3-ramnoglucosídeo e caempferol-3-ramnoglucosídeo, juntamente com 4-hidroxi-N-metil-prolina, e o éster metílico do ácido p-cumárico, foram isolados pela primeira vez das folhas de L. xuul. Os metabólitos foram identificados usando os dados espectroscópicos obtidos e pela comparação desses com aqueles encontrados na literatura.

Two new natural flavanones, 5-hydroxy-6,7-(2",2"-dimethylchromene)flavanone (1) and 5-methoxy-3-hydroxy-6,7-(2",2"-dimethylchromene)flavanone (2), were isolated from the root extracts of L. yucatanensis and L. xuul, respectively. Additionally, four known metabolites, the glycosidic flavonoids quercetin-3-rhamnoglucoside and kaempferol-3-rhamnoglucoside, together with 4-hydroxy-N-methyl-proline, and p-coumaric acid methyl ester, were isolated for the first time from the leaves of L. xuul. The various metabolites were identified on the basis of their spectroscopic data and by comparison with those reported in the literature.